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✓ Source: REIN MLS #10660299 · record updated Nov 2, 2026 · synced every 2 min · your inquiry is never resold
5037 Annapolis DR, CHESAPEAKE VA 23321 - Main photo
5037 Annapolis DR, CHESAPEAKE VA 23321 - Photo 2
5037 Annapolis DR, CHESAPEAKE VA 23321 - Photo 3
5037 Annapolis DR, CHESAPEAKE VA 23321 - Photo 4
5037 Annapolis DR, CHESAPEAKE VA 23321 - Photo 5
4beds
2baths
2,335sqft
0days on market

5037 Annapolis Dr, Chesapeake, VA 23321

New ListingResidential · built 2024 · JOLLIFF LANDING AT WESTERN BRANCH

About this home

Enjoy sought-after ranch-style living in this like-new, two-year-old Dogwood model in Estates at Joliff Landing! Located in Chesapeake's Western Branch area, this popular floor plan offers the convenience of first-floor living, with every room except the finished room over the garage on the main level. Two bedroom suites provide added flexibility, including one with a dual-entry bathroom accessible from the hallway. The upstairs bonus room offers space for a home office, media room, or guest retreat. Step outside to an oversized, fenced backyard with wooded views, a storage shed, and plenty of room to relax or entertain. Community amenities include a clubhouse, fitness room, playgrounds, and pool. Convenient to shopping, dining, military bases, and major interstates, this beautifully maintained home combines like-new appeal with an established neighborhood setting.

Listing courtesy of Bethany White · BHHS RW Towne Realty · REIN MLS #10660299

Facts & features

Type

Residential

Year built

2024

Price / sqft

$248

HOA fee

$80/mo

Taxes

$5,528/yr

County

Chesapeake VA

MLS #

10660299

HOA association includes

ClubhouseExercise RmPlaygroundsPool

$80/mo HOA fee · NONE · per the REIN MLS listing record — confirm inclusions with the association.

Interior

Bedrooms
4
Full baths
2
Approx. sqft
2,335
Stories
2
Flooring
Carpet, Ceramic, Wood
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
7
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Fin. Rm Over Gar, Foyer, PBR with Bath, Pantry, Porch, Utility Room
Appliances
Dishwasher, Dryer Hookup, Microwave, Gas Range, Refrigerator, Washer Hookup
Equipment
Cable Hookup, Ceiling Fan
Accessibility
Main Floor Laundry

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Brick,Fiber Cement
Pool
No Pool

Utilities & systems

Heating
Forced Hot Air, Zoned
Cooling
Central Air, Zoned
Water heater
Gas
Water
City/County
Sewer
City/County

Lot, parking & ownership

Lot size
0.1900
Subdivision
JOLLIFF LANDING AT WESTERN BRANCH
Zoning
RES
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Multi Car, Off Street, Driveway Spc
Possession
CLOSING
Disclosures
Common Interest Community, Disclosure Statement, Resale Certif Req

Sources: REIN MLS record

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

5037 Annapolis Drive is a 2024-built, four-bedroom home in Chesapeake, Virginia. It sits in the 23321 zip code, close to dining, coffee, and fitness options. Two major military installations are each about 17 minutes away. There is a lot to like about this address.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23321, homes for sale zoned for Western Branch High School, and homes for sale zoned for Western Branch Intermediate School. Nearby, look at Western Branch homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

Built in 2024, this home brings 2,335 square feet of fresh construction to a Chesapeake address that punches well above its size. Four bedrooms and two full baths give you real room to spread out. The year of construction means systems, finishes, and materials are all brand new. That combination — new build, generous square footage, and a location inside the 23321 zip code — is harder to find than it looks.

JOLLIFF LANDING AT WESTERN BRANCH and the Chesapeake real estate market

Annapolis Drive sits in the western reaches of Chesapeake, in the 23321 zip code. This corner of the city has a suburban feel with wide streets and newer residential development. Neighbors here tend to keep tidy yards, and the pace is relaxed without feeling remote. Western Branch is one of Chesapeake's most established communities, with a mix of established homes and newer builds side by side. The area connects quickly to both Portsmouth and Suffolk via Route 17 and Interstate 664. Chesapeake itself is Virginia's second-largest city by land area, so open space is never far. Downtown Norfolk is roughly 25 minutes east, and Virginia Beach is about 30 minutes away. Everyday errands stay local thanks to Chesapeake Square Mall and a dense retail corridor along Airline Boulevard. Commuters appreciate the multiple highway options that fan out from this part of the city.

What's nearby

Coffee is a two-minute walk away — Starbucks Coffee Company is just 0.2 miles from the front door. Half a mile out, Branches Tasting Room offers a relaxed spot for an evening out. Fruitsplash Factory and Gather Cafe round out the nearby food-and-drink scene at 0.5 miles each. Fitness options are equally close. Onelife Fitness at Chesapeake Square Gym is 0.7 miles away, and the National Personal Training Institute is the same distance. Candlewood Suites Chesapeake/Suffolk also has gym access at 0.5 miles. Daily life is easy here.

For different buyers

Base commute and VA loan notes

Naval Medical Center Portsmouth is about 17 minutes from this address. Norfolk Naval Shipyard is the same drive time in a different direction. VA loan financing is common in this part of Chesapeake, and a 2024 build means no deferred maintenance to negotiate around. That combination of dual-base access and new construction is genuinely useful for anyone weighing a PCS move to this area.

For first-time buyers

A brand-new 2024 build means everything is under warranty and nothing needs fixing before you settle in. Four bedrooms give you flexibility — a home office, a guest room, and still have space left over. The 23321 corridor has solid infrastructure and easy highway access. Anyone comparing homes for sale zoned for Western Branch High School or homes for sale zoned for Western Branch Intermediate School will find this address lands squarely in that zone.

More buyer questions

How far is 5037 Annapolis Drive from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is about 17 minutes from this address under typical traffic conditions. Norfolk Naval Shipyard is also roughly 17 minutes away in a separate direction.

What year was 5037 Annapolis Drive built?

The home was built in 2024, making it a true new construction. All major systems and finishes are brand new.

Is 5037 Annapolis Drive in a flood zone?

Flood zone information for this address is available in the FloodRisk tile on this page. Review that section for the current FEMA designation.

How many bedrooms and bathrooms does 5037 Annapolis Drive have?

The home has four bedrooms and two full bathrooms across 2,335 square feet of living space.

Where is 5037 Annapolis Drive located in Chesapeake?

The address sits in the western part of Chesapeake in the 23321 zip code, near the Western Branch community and close to Route 17 and Interstate 664.

Tom and Dariya Milan at LPT Realty know this part of Chesapeake well. Reach out to get your questions answered and schedule a closer look at 5037 Annapolis Drive.

Summary generated by AI from public records and publicly available information.

How Far Is?

Driving distance by road and typical drive time via Google Maps, to the nearest location of each.

Also nearby

Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.

Homes like this one sell fast — see the next one first

Chesapeake$490K – $670K4+ beds

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Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

Flood Risk

Looking up FEMA flood zone…

Explore this neighborhood

Western Branch

Western Branch is a home neighborhood in Chesapeake, Virginia. It has tree-lined streets and a mix of single-family homes. The area shares the wider suburban feel of Chesapeake.

$380K

Median sale · 12 mo

$202

Sold $/sq ft

33d

Days on market

46

For sale now

$95K

HH income

72%

Owner-occupied

REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year

Explore Western Branch →
Map of Western Branch with neighborhood boundaryNeighborhood

homes for sale in Chesapeake →

Military Commute

Drive times to nearest bases

NMCP

Navy

18min·12.3mi

NNSY

Navy

16min·11.9mi

USCG Portsmouth

Coast Guard

18min·13.2mi

J7 Suffolk

Joint

20min·11.7mi

NSA HR

Navy

33min·20mi

Drive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.

The numbers

Payment Calculator

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$3,634/mo

Principal & interest

$3,004

Property tax

$461

Home insurance

$169

PMI

None

HOA/Condo (paid separately)

$80

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.

Value & history

Comparables

Price context — similar nearby homes

$480,000 – $600,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

1905 Old Jolliff RD · 1 mi · 2,261 sqft$480,000 sold 2026-06
4936 Oriole DR · 1.2 mi · 2,378 sqft$535,000 sold 2026-10
4737 Condor DR · 1.3 mi · 2,350 sqft$600,000 sold 2026-08

Own a home nearby? See what it is worth today — What's your Chesapeake home worth?

Sale & Tax History

List Price

$579,000

Price / Sq Ft

$248

Annual Taxes

$5,528

Monthly Tax

$461

HOA fee

$80 / mo

Tax Rate (effective)

0.95%

Sale Timeline (this listing)

EventDatePriceDetail
ListedNov 2, 2026$579,000—
Currently listed—$579,000—

Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:

Chesapeake Real Estate Assessor

Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.

Comparable Properties

Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.

Market tempo

0 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Is 5037 Annapolis Dr in a good school zone?+
The assigned zones on the listing record are Western Branch Intermediate (VaHome School Score 6.2/10), Western Branch Middle (VaHome School Score 6.8/10), Western Branch (VaHome School Score 6.3/10). School attendance zones can change — always confirm enrollment with the local school division.
Does 5037 Annapolis Dr have an HOA?+
Yes — HOA dues are on record for this property (the current amount is shown in the facts section on this page). The association of record is NONE. Association amenities on record include: Clubhouse, Exercise Rm, Playgrounds, Pool.
When was 5037 Annapolis Dr built?+
It was built in 2024, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

Brokered by LPT Realty · Hampton Roads

Listing courtesy of Bethany White · BHHS RW Towne Realty · REIN MLS #10660299

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

Schedule a private tour

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5037 Annapolis Dr, Chesapeake — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

5037 Annapolis Dr, Chesapeake, Virginia 23321 · MLS #10660299 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.

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